Top Tech Jobs & Startup Jobs in Calgary

Lead and resolve high-severity post-sales technical escalations through deep-dive investigation, reproduction, and engineering handoff. Own customer calls, collect logs/evidence, file bug reports, monitor patterns, and improve tooling and runbooks in partnership with Support and Engineering.

Partner with Account Executives to drive new commercial business by leading technical discovery, solution architecture, demos, and POCs. Co-own pipeline, guide complex multi-stakeholder deals, provide product and GTM feedback, and build scalable enablement resources and demo environments for the SE team.

Lead the dataplane product vision and roadmap, spanning WireGuard, DERP, relays, subnet routers, exit nodes, and connectors. Define customer-facing performance and reliability SLOs, drive regional capacity and relay operations, own operator tooling and admin/CLI surfaces, partner across engineering, GTM, and customers, and represent Tailscale externally on dataplane strategy and deployments.

Work on an AI-native Strategic Projects team to turn prototypes (LLM gateways, proxies, sandboxes) into production-grade services. Own hardening, error handling, observability, operational tooling, security review practices, and customer integrations. Use coding agents and LLMs heavily, collaborate with product-minded engineers and reference customers, and ensure prototypes meet production reliability and maintainability standards. Remote role with light travel (<10%).

Owner of the developer experience for Tailscale-native apps: define reference architectures, SDK and CLI product strategy, improve onboarding and docs, run internal dogfooding, partner with engineering and GTM, and engage external developers to drive adoption.